How DigitalOcean built a design team.

When DigitalOcean first deployed Califa, it was issued a broken old MacBook Air and a vague task for the week. The first commit landed the next day. Real impact took months, because nobody had explained the lay of the land. New designers got a better start. Onboarding covered:

• The design team’s values, recently written down.
• How the design team and the company worked, the tools they used, and access to the right software and Slack channels.
• Training and starter tasks in Buoy, the design system.
• A deep dive into every current and future product, and how they fit together.
• An overview of every team design worked with, and how to work with each one.
• Meetings with the people they’d work with most, such as PMs and EMs.

Getting a designer to build quickly is easy. Getting them to build the right thing quickly is harder. New designers were up and running within two weeks, with enough context to do great, high-impact work.

DigitalOcean had a strong learning culture, and growing each designer was a core part of the deployment. One UI Designer trained in UX methods and took on more complex projects over a year, until he earned the Product Designer title. A designer interested in management got regular mentorship, a stint leading the team, and then a promotion to lead the Brand Design team full-time. Another designer later took a similar path and went on to lead a Product Design team.

Other designers wanted to grow through their projects. Some wanted more variety or meatier UX work. Others wanted to run Design Sprints, spend more time on research, own the design system, or get better at Framer. Califa found a path for each of them while keeping every in-flight project covered. A designer who isn’t showing up on one project can be extremely productive on another.

The team’s work was good but not great. It wasn’t ambitious enough, for a few reasons:

• Engineering was short-staffed, so most projects were scoped down.
• Before the Product org found its footing, projects often changed several times mid-process.
• Buoy, the CSS style guide, made the platform consistent. Left unchecked, it also made it harder to try anything new.

Designs were usable but not compelling. They followed established patterns even when they shouldn’t have. The team had the skills to do much better and needed a push, which came in four parts: a process checklist, regular design reviews, regular design jams, and a new process for updating design patterns.

Califa started hour-long critiques three times a week, which later became half-hour critiques every day. They followed standard practice. Laptops and phones down. One designer facilitates and takes notes. The presenter gives context, shows the work, and says what kind of feedback they want. Everyone else asks questions and gives feedback. The group then recaps the notes and writes next steps, usually to resolve specific issues or explore part of the design. The presenter is held to those steps at their next review.

Reviews also became where the team worked with Brand Design on brand changes, illustrations, and color palettes headed for the product. Califa attended almost every review as a fellow designer, not a manager with extra authority, and pushed every time for more exploration, better reasoning, closer attention to detail, and more ambitious work. Soon the designers were pushing each other for the same things. Regular design reviews did more for design quality than anything else the team tried.

Later that year, some designers moved out of the design pod to sit with their PMs and engineers. The team lost the collaboration that happens when two designers’ screens are side by side, and asked for a fix. The fix was a weekly design jam. Designers signed up to bring a problem and work through it at a whiteboard with the rest of the team.

Together, these four changes made the team more enthusiastic, more ambitious, and noticeably better at its work.

That left trust. The design team had always been close-knit, with a great culture. It was also siloed. The team produced a lot of great work, and other departments saw it too late. The company stopped trusting design. People didn’t know what the team was working on, and when they found out, they didn’t know why. The platform and network engineers who built the technology had no part in deciding how customers would use it. Leadership wasn’t involved in most of the design process, so it wasn’t invested in the results.

Design was also missing perspectives it needed, sometimes ones that decided whether a product was viable at all. Support would see a design in production and point out that it wouldn’t survive fraud. Engineers would see a design several rounds in and add context that changed the product. Leadership would see designs late and cut whole features, and the team would scramble to ship something worse instead of a thoughtful MVP. It was the design team’s responsibility to change that. It had left working with the rest of the company to other people and focused on the work. Two initiatives fixed it.

Sessions followed a set structure:

• 10m: The Product Designer explains the problem
• 10m: Sketch session (everyone sketches, not just designers)
• 10m: Each person explains their sketches (2m per person)
• 5m: Each person lists what they liked most about other designs (1m per person)
• 25m: Repeat the last three steps

Afterward, the designer picked the ideas with the most potential and turned them into a first prototype. Studios didn’t produce a final design. They did four other important things:

• They brought in valuable perspectives that led to better solutions.
• They spread context and opened a line to engineering that stayed open for the rest of the project.
• They shared ownership of the design, which meant less friction during the build and engineers who felt more connected to the product. One senior engineer who had been at the company for years said it was the first time they’d had any say in the interface, and that it felt amazing.
• They built trust in Product Design by showing colleagues what the team actually does.

The team never treated craft as something only designers could do. With the right guidance, anyone can take part. Califa had hired designers who valued collaboration and left their egos at the door. They just hadn’t had a channel for it. Design studios became the standard way to start a project.

That said, design studios don’t scale to 300 people. Leadership needed more visibility into the process, and design still needed a way to build trust with the entire company, keep every potential stakeholder informed of progress and let them step in where needed, and tap into knowledge from every part of the company.

Replies came from nearly every department, including Engineering, Support, People, Finance, Community, Product, Brand, Customer Success, and Sales, and from every level, interns to the CEO. Everyone felt involved in the design process, and the company came to trust design with the product. Some of the replies:

• “This is the best-designed email I’ve gotten in my inbox. Well done.”
• “Good stuff, Joel. I sit right next to you and I know more now about what you do than I ever have!”
• “This is amazing! Thanks for putting it together, and for the great designs.”
• “How do I subscribe to this or is this something you plan to send out weekly, monthly?”
• “Top notch content as always, I really enjoy reading through these”
• “Wonderful as usual, thanks for the updates. I like how you shouted out certain people from other departments, nice touch Joel-san.”
• “LOVE the wireframes!!! HURRAH for rapid prototyping and moving fast!”

Others brought questions and feedback that helped other teams build the right supporting technology. The company learned what kind of feedback helps, so designers got useful feedback every time a Gazette went out. People looked forward to it, and asked about it when an issue was late. It became one of the main ways people found out where new products stood, even in Engineering. Most importantly, it convinced the company that Product Design knew what it was doing.

In its time leading Product Design at DigitalOcean, Califa doubled the team and put processes in place that helped each designer do their best work. The team became tight-knit and high-performing, and was known across the company for how healthy it was. Regular transparency earned Product Design more trust and more leeway across the board.

None of these processes were meant to restrict anyone. They added structure where structure was needed. The team usually designed them together, and most of them stuck because the designers liked them. Califa ran the team hands-off. It hires good people and gives them room. It clears roadblocks, breaks ties, helps with personal development, and is there to talk. It pushes back when the team can do better, on output, ambition, or quality. It does not design for them.

Califa didn’t design the products DigitalOcean shipped in that period. Its team did, and Califa made sure they could.

Califa has run the same practices in later deployments. At Heap, a quarterly company-wide deck gave every usability improvement its own slide. At Unify, leadership got 18 written updates in two quarters.